While You Were Sleeping
by EmilyStark
Summary: AH In a coma after being saved by Elena, Stefan is virtually a vegetable laying in a bed. Elena has been drooling over her boss for the past four years, and when he falls onto the train tracks one morning, she saves him from the oncoming train. Everything changes when a nurse calls her his fiancee, and Stefan's family comes into the picture, plus charming Damon. Things will change.
1. Summary

**While You Were Sleeping**

**By EmilyStark**

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**Summary**

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In a coma after being saved from being hit by a train by a beautiful brunette, Stefan Salvatore is virtually a vegetable laying in a bed.

Ever since she first laid eyes on the wealthy businessman, Elena Gilbert always dreamed of him loving her the way she had grown to love him, even if only through being his personal assistant for the past four years. And while accompanying him to the train station, she witnesses from afar Stefan lean a little too far over the side of the platform and fall straight onto the tracks, knocking himself unconscious. It's her time to take action for the love of her life.

One mishap leads to another when a nurse informs a doctor that Elena is Stefan's fiancée, but eventually, she begins to like the sound of it. Maybe there's a chance for her finally being able to love the man she had been drooling over.

That is, until she meets his family, and his estranged, wicked brother, Damon.

Affairs will begin…

Secrets will barely be withheld…

Everyone's lives are going to change…

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**A/N: I will post the first chapter later on... tell me how you think it will be!**


	2. Stuck On You

**A/N: Disclaimer: I do not own the characters affiliated with the television show, the Vampire Diaries. All rights belong to Kevin Williamson & Julie Plec. I kindly ask not to steal any of my writing, however.**

**Don't forget to check out the story's picture! ;)**

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Her breath shook, emitting clouds of pallid mist into the darkened area. The streets crept with homeless citizens and the reverberations of the shouts of the temporarily displaced, the passing buildings' walls with ears soaking up each note. Obscene words spewed her way went unnoticed as she continued down the walk, the dark purse gripped tightly within the clutches of her bony hands. The worn blue jacket weighed heavy on her slumped shoulders, her head bowed slightly.

She couldn't wrap her around as to why she absolutely _had _to come into work at five in the morning when the company's guard arrived at five-thirty.

Tapping her foot impatiently outside the cream shaded building, her eyes continuously glanced down at her wrist to her watch, slung so precisely on her bony wrist. The face of the clock glimmered in the dull light from above, indicating the exact time of six-fifteen. Four years of coming in early, four years of waiting in the freezing cold or scolding hot city air, four years of wanting to punch the lights out of her boss, four years of following commands, four years of secretly falling for the same man that barely acknowledged her except for asking when the coffee would arrive. Four years of the same bullshit.

_I need a vacation._

Her eyes caught sight of a beat-up Ford high-tailing around the corner, barely escaping clipping the metal edge of the stop sign. She could practically see the smirk playing on his lips even with his dark, tinted windows. The car barreled forward, tires screeching as it came to a shrieking halt below the canopy. Rolling her eyes, she leaned against the wall of the building. The ticking hands on the watch indicated he was severely late, practically worthy of a canning.

The door to the Ford swung open, and out came the bumbling dirty-blonde. His eyes flickered up to her, face etched with repentance. She shook her head before pointing towards the crown of his. He stopped mid walk and spun around to the opened door of his car. Reaching in, he quickly grabbed the uniform hat and shoddily pushed it onto his head.

Elena felt a pang of sorrow for the poor man. He worked for one of the wealthiest law firms in the city, yet they refused to supply him with a suitable uniform. His hat barely fit the entirety of his head, his suit clung too tight, and his shoes looked as if they were about to burst, which must be a pain for his feet. They didn't even supply with him with any weapons, dammit. The head supervisor of security claimed 'the security officers should use hand-on-hand combat when faced with danger.' The man before her needed to seriously rethink this job.

He straightened his back, flashed a small smile and rushed towards the door. Before he could enter the building, she quickly reached out and grabbed the sleeve of his jacket. He spun around, surprised by her sudden actions.

"One sec," She muttered before rifling through her purse. Her fingers wrapped around the silk, red tie and pulled it out. His eyes widened slightly, glancing frantically down to where his tie would normally be. She gripped his hand and forced the tie into his grip. "You always forget one tiny detail, Matt," She chuckled, clapping him on the shoulder. He let out a laugh, then secretly breathing a sigh of relief.

The tumbles in the keyhole jingled before clinking into place, allowing the two of them access to the darkened building.

"He still has you coming in this early?" Matt asked, his tight dress shoes squeaking towards the security room. She sighed, trying her best to keep with him as he walked with rapid speed.

"Yup. Been doing this for four years, and it's never going to end." Her eyes squinted shut when he managed to locate the main light switches. The flickering lights above came to life, pouring light into the dark room.

He plopped into the chair, staring uneasily at the creepy screensaver on the computer, "You've been doing this for too long. Plus the guy's a douchebag. You could do so much better than this lousy job."

She chuckled, setting her purse on the table beside the computer and settling into the swivel chair in the corner. A moan of gratitude escaped her when her sore back hit the cushion of the chair, "I could say the same to you, too."

He spun around in the chair, short hair blowing in the light breeze. He reminded her of a child, a child stuck in a grown man's body, "Nah, I like my job."

"You _like _it?" She crossed her arms, narrowing her eyes slightly.

Spinning in a complete circle, he suddenly stopped when there was a beeping noise from one of the security monitors. Using his feet to pull the chair towards the monitor, he carefully zoomed in, turning on the emergency light to scare away any possible intruders. After locating nothing but a stray, skittish cat he spun back around to face her, "When I was a kid, I wanted to be an astronaut. Course, those dreams were crushed when I discovered that I was claustrophobic. So I thought and thought. For years I just thought of how I could contribute to the world. Then nine-eleven happened, and as I was watching those two towers fall, I knew that I wanted to protect my country. My mother wouldn't allow me to enlist in the armed forces so once I hit eighteen, I traveled to New York and found a job where I could protect at least one building." He shrugged his shoulders, turning his gaze towards the clock, "You should probably get going. Boss will be here soon."

She nodded numbly, astounded by his background story. She never knew that she wasn't the only one in the building emotionally affected by the events of September 11th. Boss never really showed any emotions, not to her anyways. He was either Normal Boss or Angry Boss. And Elena had grown to know his quirks all too well that she knew exactly what ticked him off. Grabbing her purse, she muttered a brief farewell before stomping towards the elevator.

* * *

The coffee room was located on the sixth floor, stuck in the middle of conference room number eight and the main copy room. She was running on a tight schedule today: grab Boss' coffee, copy the twenty-page brief on the Donald case, and prep conference room number thirteen for the one o'clock meeting. Huffing out, she pressed down the black button before scurrying over to the copy room. Thirteen minutes until the coffee is ready, and the copying of the brief should take about seven minutes as long as the machine doesn't jam like it did last week, leaving sixteen minutes for her to prep the conference room. Yeah, she should make it to her desk by seven.

Quicker than her dead grandmother could say jalapeño sauce, she located the brief in her briefcase (which is always left at her desk) and set the copier to the maximum speed. Inserting the brief, she leaned against the table, tapping her manicured nails. Within seconds, the machine began shooting out clones of the original. The loud, obnoxious beeping from the coffee room sounded, indicating that the coffee was finished.

Grabbing the finished copies as well as the original, she stuffed them into her briefcase then ran into the neighboring room. She set her briefcase beside the machine, and carefully took the mug out of the appliance. It left a significant red mark on the webbing between her thumb and pointer, but she's been dealing with it for the past years. The clinking of the bottom ring of the mug against the marbled counter sounded pleasant to her ears as she set about preparing the perfect cup of joe. It seemed to be the only thing Boss complimented her on.

With a sigh, she carefully picked up the mug as well as her briefcase and rushed towards the elevator to begin prepping the conference room.

* * *

"Elena!" The deep voice boomed, reverberating around the large office twice over. Her head snapped up, eyes finally opening. _Crap_, she thought, _had I really fallen asleep?_

A menacing smirk was playing on his lips, one that had her weak in the knees, "Falling asleep on the job, are we now?" She rubbed her eyes, a yawn accidentally pushing its way through.

She stood to attention just like every other morning, "My apologies, Boss." Her hands fumbled to flatten her bunched skirt. He nodded stiffly and began to walk towards the large oak doors leading to his office. She perked up, remembering a mental note she had taken, "Sir," he glanced over his shoulder, "I thought we were on a last name basis."

His shoulders rose to give a half-assed shrug, "I guess so, Elena." He gave a playful, yet stimulating wink before sauntering into his office. She collapsed into her swivel chair, her breath erratic. That was the sixth time this week he winked at her. _Maybe he feels the same way I do about him_, she thought with a glimmer of hope.

Gripping the pen firmly in her shaking hand, she began to write the outline for the next meeting on the Donald case. No matter how much effort she put into attempting to focus on her work, her mind kept traveling to his little performance before. He winked! She couldn't help but mentally squeal. It was a breakthrough, as well as a much needed self-esteem boost.

Boss, she so badly wanted to call him Stefan, held a poor track record with women. He had the most beautiful women in his grasp, and when it got too serious for him, he cut all of the strings. She had hopes that if they ever became an item, he would be different for her. _Yeah right_, she thought, _he would have to be hit in the head with a rock to knock some sense into him. _

If she ever needed a boost of hope on them someday becoming a couple she would look towards his father. Giuseppe Salvatore: playboy turned family man thanks to Martha, his longtime wife. She knew of the Salvatore's having only one son, Stefan, but the way he said it had her highly doubting it. Maybe there was a disowned child? Her head spun from the possible scenarios.

"Elenaaaa," A voice came in over the callbox, obviously irritated. There was a shuffle of papers, then silence.

She pressed the silver button in the center, "Yes, sir?"

There was pause before he continued, "You wouldn't happen to know where my coffee is, would you?" A blanket of sheer panic overcame her as she quickly darted her eyes around the vicinity.

Pressing the button, she replied, "Yes I do, sir. I'll bring it right in." The line went silent, thankfully. Out of the corner of her eye, she spotted the black mug with the words 'Like A Boss' printed in red across the front. Sighing in relief, she plucked it from the desk and dashed towards the oak doors. She knocked thrice before there was a clearing of the throat.

"Come in."

She pushed the door open with her free hand, careful not to spill any of his 'precious' coffee. He glanced up from typing on his laptop, even if he knew that she didn't buy his charade. There was a 98% chance that he was chatting with some random blonde on Skype, which really had ruffled her feathers in annoyance. Setting the cup on the spot specially reserved for his mug, she glanced up with a small, faux smile playing on her lips.

"Will that be all, sir?" She asked, eyes locked to his. He shifted uneasily, directed his gaze to his laptop and nodded. Spinning on her heels she sauntered back to her desk to insipidly fill out more briefs.

* * *

Lunch break arrived quicker than she had imagined. The small timer on her desk rang gallingly, indicating that it was time for her to get the hell out of that office. Filing away her papers, she sighed in content. Just as she stood, the doors to Boss' office flung open with a _crash! _She rolled her eyes, knowing that she would have to purchase more lamps now. She grabbed her purse, glancing up uneasily at her boss who stood motionlessly with a content smile playing on his lips.

She nearly jumped clear out of her skin when he threw his hands up in the air and exclaimed, "God, I can't wait to get out here!" Without another word he strolled towards the elevators and jabbed endlessly at the bottom arrow. Elena followed suit, slinging her purse on her shoulder and walking silently after Boss.

The metal doors slid open, revealing an empty, glass-clad elevator. He jumped inside with childlike giddiness. Elena huffed, trying her best to catch up before the doors closed. Giving up all hope, she stopped, deciding to wait until the elevator came back up. He stopped rocking on his heels, seeing through the rapidly closing crack in the doors the deep frown placed on her adorable little face. He swiftly stuck his right hand through the space in-between.

She glanced up, surprisingly hearing the doors slide back open. There stood Stefan, in all his wealthy glory, smiling generously at her. She smiled back before rushing inside to beat the closing doors.

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The ride downstairs was silent with the exception of Stefan clicking his tongue in impatience. Once the doors slithered open he shot out of the elevator so fast she began to believe that he had superpowers. Gripping the strap of her purse tighter she walked towards the rotating doors, head hung low.

She knew exactly where he was going; the D train since it will take him to East Side where his penthouse apartment was located. She happened to live a few blocks away from his apartment building in a cozy little apartment with her cat, Athena. Ever since discovering that they traveled on the same subway, she would quietly sneak onto the train with hopes that he wouldn't spot her. Though there were multiple times that he nearly recognized her.

Wrapping her jacket further around her, she cursed herself for not wearing a heavier one. She watched as he quietly slipped into a crowd, disappearing so easily. It amazed her how he could fit right into a swarm of people. _Almost like a chameleon_, she mused.

* * *

She rested her feet on the seat directly next to her, not caring if there were multiple, standing people glaring her way. Her hood was pulled over her head, as she did every other day, not wanting to risk a chance of Stefan seeing her. It would be so awkward, and he would most likely consider her a stalker if he found out that she purposely moved to East Side because of him.

It's not that she doesn't like the East Side, she does. It's just that she never favored the wealthier neighborhoods of Manhattan. She was constantly running into snobs. At least it wasn't like her old neighborhood where there would be a drive-by shooting every week.

She huddled her arms to her chest, suddenly feeling freezing. She glanced up to see if the air conditioning had been turned on. To her utter horror, she saw the face of her boss, quietly reading the newspaper. Her face turned a bright shade of red before she directed her gaze to her lap. Thankfully, he hadn't seen her jerky movements.

The announcer's voice rung throughout the train, announcing, "First Avenue is coming up."

She rose to her feet, careful to keep her head low. The crinkling of a newspaper had her rushing her movements, making her way to the doors. It seemed as if forever before the doors glided open, allowing her to step out.

Ever so slowly, she glanced over her shoulder to see him just stepping off of the train. Turning back around, she continued on her way home, taking note of where her pepper spray was placed in case she bumped into the wrong crowd.

* * *

"Good morning, Miss Sunshine." Matt greeted, tipping his hat painfully with a mischievous smirk. I smiled back, recovering from the shock of the front doors being unlocked and the lights to the building switched on. He could see the questioning look in her eyes, and shrugged. Suddenly, he jerked his gaze away from her and to the doorway. The smile immediately disappeared before he straightened his back.

Elena flashed a quizzical look his way. She followed his gaze, finding the towering figure of Stefan, briefcase gripped in his grasp.

"Donovan, shouldn't you be watching the monitors?" His voice boomed, sending chills down her spine. She's never heard him use that tone before, and it frightened her. Matt nodded and swiftly entered the security room.

Stefan's gaze idled on the security room door, then darted towards her still face. His lips were drawn into a deep frown as he mumbled, "I'm guessing that nothing is prepared yet," She shook her head numbly, "Very well. I will be in my office if you need me." Her eyes remained locked on his figure as he silently entered the elevator.

She swallowed the lump that had formed in her throat, feeling realization suddenly dawning on her that she has a tight schedule ahead of her, just as every day for the past four years. She had no idea, for the sake of her sanity, how she continues to drool over that careless playboy.


End file.
